82589-55-7

Upstream product

• 50-00-0 formaldehyd 
• 7568-93-6 2-Amino-1-phenylethanol 
• 87664-51-5 N-(3,4-Dimethoxybenzoyl)-2-pyrrolidincarbonsaeurebenzylester 
• 87664-54-8 N-(3,4-Dimethoxybenzyl)-2-pyrrolidincarbonsaeure-hydrochlorid 
• 87664-53-7 N-(3,4-Dimethoxybenzyl)-2-pyrrolidincarbonsaeurebenzylester 
• 93-07-2 Veratric acid 
• 16652-71-4 benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride 
• 108-24-7 acetic anhydride 
• 87664-56-0 2,3-Dimethoxy-10-hydroxy-5,7,8,9,9a,10-hexahydro-pyrrolo<1,2-b>isochinolin 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 82590-36-1 (Z)-5-(3,4-Dimethoxy-phenyl)-4-nitro-pent-4-enoic acid ethyl ester 
• 82589-49-9 2-(3,4-Dimethoxy-benzyl)-pyrrolidine-1-carbaldehyde 
• 82590-44-1 4-Amino-5-(3,4-dimethoxy-phenyl)-pentan-1-ol 
• 66162-43-4 2-(3,4-dimethoxy-benzyl)-pyrrolidine 

Relevant academic research and scientific papers

Friedel-Crafts Acylation with N-(Trifluoroacetyl)-α-amino Acid Chlorides. Application to the Preparation of β-Arylalkylamines and 3-Substituted 1,2,3,4-Tetrahydroisoquinolines

Several N-(trifluoroacetyl)-α-amino acid chlorides have been reacted with benzene, anisole, and veratrole in the presence of AlCl3 or SnCl4 to produce the corresponding aromatic ketones in fair to high yields.The products are reductible under neutral or acidic conditions to the corresponding N-(trifluoroacetyl)-β-hydroxy-β-arylakylamines or N-(trifluoroacetyl)-β-arylalkylamines.The latter can be readily detrifluoroacetylated by mild basic hydrolysis and thence converted to the corresponding 3-substituted 1,2,3,4-tetrahydroisoquinolines by condensation with formaldehyde.

Electron-Impact Induced Loss of C-5/C-8 Substituents in the Molecular Ions of 1,2,3,4-Tetrahydroisoquinolines, I: Synthesis of a 4-Acetylpyrroloisoquinoline

The synthesis of the 4-acetylpyrroloisoquinoline 3 is described.

Synthesis of Hexahydropyrroloisoquinolines - Analogs of Phenanthroindolizidine Anticancer Alkaloids

A convenient preparative route has been developed for the synthesis of hexahydropyrroloisoquinolines involving condensation of an araldehyde with ethyl 4-nitrobutanoate followed by LAH reduction and subsequent cyclization with H2SO4 to 2-arylmethylpyrrolidines.The latter on formylation and Bischler-Napieralsky cyclization followed by NaBH4 reduction give the required pyrroloisoquinolines.Using this method, 8-methoxy-1,2,3,5,10,10a-hexahydropyrroloisoquinoline (IXa); 7,8-dimethoxy-1,2,3,5,10,10a-hexahydropyrroloisoquinoline (IXb); 7,9,10,11,11a,12-hexahydrobenzopyrroloisoquinoline (Xa); 3-methoxy-7,9,10,11,11a,12-hexahydrobenzopyrroloisoquinoline (Xb); 7,7a,8,9,10,12-hexahydrobenzopyrroloisoquinoline (XIa); 3-methoxy-7,7a,8,9,10,12-hexahydrobenzopyrroloisoquinoline (XIb) and 2,3-dimethoxy-7,7a,8,9,10,12-hexahydrobenzopyrroloisoquinoline (XIc) have been synthesized.None of these compounds has shown any noteworthy anticancer activity while few have exhibited interesting antihistaminic, β-blocking, hypertensive, antiinflammatory and antireserpine activities.